Literature DB >> 14759192

Mechanistic investigation leads to a synthetic improvement in the hydrolytic kinetic resolution of terminal epoxides.

Lars P C Nielsen1, Christian P Stevenson, Donna G Blackmond, Eric N Jacobsen.   

Abstract

The mechanism of the hydrolytic kinetic resolution (HKR) of terminal epoxides was investigated by kinetic analysis using reaction calorimetry. The chiral (salen)Co-X complex (X = OAc, OTs, Cl) undergoes irreversible conversion to (salen)Co-OH during the course of the HKR and thus serves as both precatalyst and cocatalyst in a cooperative bimetallic catalytic mechanism. This insight led to the identification of more active catalysts for the HKR of synthetically useful terminal epoxides.

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Year:  2004        PMID： 14759192     DOI： 10.1021/ja038590z

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  24 in total

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Journal:  J Am Chem Soc       Date:  2011-04-22       Impact factor: 15.419

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4.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

5.  A green chemistry approach to asymmetric catalysis: solvent-free and highly concentrated reactions.

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6.  "Cassette" in situ enzymatic screening identifies complementary chiral scaffolds for hydrolytic kinetic resolution across a range of epoxides.

Authors:  Sangeeta Dey; Douglas R Powell; Chunhua Hu; David B Berkowitz
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Synthesis and field evaluation of stereoisomers and analogues of 5-methylheptadecan-7-ol, an unusual sex pheromone component of the lichen moth, Miltochrista calamina.

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Journal:  J Chem Ecol       Date:  2014-03-15       Impact factor: 2.626

8.  Mechanistic Studies Inform Design of Improved Ti(salen) Catalysts for Enantioselective [3 + 2] Cycloaddition.

Authors:  Sophia G Robinson; Xiangyu Wu; Binyang Jiang; Matthew S Sigman; Song Lin
Journal:  J Am Chem Soc       Date:  2020-10-16       Impact factor: 15.419

9.  Synthesis of (+)-sch 642305 by a biomimetic transannular Michael reaction.

Authors:  Barry B Snider; Jingye Zhou
Journal:  Org Lett       Date:  2006-03-30       Impact factor: 6.005

10.  Mechanistic basis for high stereoselectivity and broad substrate scope in the (salen)Co(III)-catalyzed hydrolytic kinetic resolution.

Authors:  David D Ford; Lars P C Nielsen; Stephan J Zuend; Charles B Musgrave; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2013-10-07       Impact factor: 15.419
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